diff --git a/Lib/ipaddress.py b/Lib/ipaddress.py
index 1f900583826a80..35ca38e54fe214 100644
--- a/Lib/ipaddress.py
+++ b/Lib/ipaddress.py
@@ -1410,7 +1410,8 @@ def __lt__(self, other):
         if address_less is NotImplemented:
             return NotImplemented
         try:
-            return self.network < other.network
+            return (self.network < other.network or
+                    self.network == other.network and address_less)
         except AttributeError:
             # We *do* allow addresses and interfaces to be sorted. The
             # unassociated address is considered less than all interfaces.
@@ -2100,7 +2101,8 @@ def __lt__(self, other):
         if address_less is NotImplemented:
             return NotImplemented
         try:
-            return self.network < other.network
+            return (self.network < other.network or
+                    self.network == other.network and address_less)
         except AttributeError:
             # We *do* allow addresses and interfaces to be sorted. The
             # unassociated address is considered less than all interfaces.
diff --git a/Lib/test/test_ipaddress.py b/Lib/test/test_ipaddress.py
index 91ae8d85edfc21..e3dec87ed990f7 100644
--- a/Lib/test/test_ipaddress.py
+++ b/Lib/test/test_ipaddress.py
@@ -1404,14 +1404,35 @@ def testAddressComparison(self):
                         ipaddress.ip_address('::2'))
 
     def testInterfaceComparison(self):
-        self.assertTrue(ipaddress.ip_interface('1.1.1.1') <=
-                        ipaddress.ip_interface('1.1.1.1'))
-        self.assertTrue(ipaddress.ip_interface('1.1.1.1') <=
-                        ipaddress.ip_interface('1.1.1.2'))
-        self.assertTrue(ipaddress.ip_interface('::1') <=
-                        ipaddress.ip_interface('::1'))
-        self.assertTrue(ipaddress.ip_interface('::1') <=
-                        ipaddress.ip_interface('::2'))
+        self.assertTrue(ipaddress.ip_interface('1.1.1.1/24') ==
+                        ipaddress.ip_interface('1.1.1.1/24'))
+        self.assertTrue(ipaddress.ip_interface('1.1.1.1/16') <
+                        ipaddress.ip_interface('1.1.1.1/24'))
+        self.assertTrue(ipaddress.ip_interface('1.1.1.1/24') <
+                        ipaddress.ip_interface('1.1.1.2/24'))
+        self.assertTrue(ipaddress.ip_interface('1.1.1.2/16') <
+                        ipaddress.ip_interface('1.1.1.1/24'))
+        self.assertTrue(ipaddress.ip_interface('1.1.1.1/24') >
+                        ipaddress.ip_interface('1.1.1.1/16'))
+        self.assertTrue(ipaddress.ip_interface('1.1.1.2/24') >
+                        ipaddress.ip_interface('1.1.1.1/24'))
+        self.assertTrue(ipaddress.ip_interface('1.1.1.1/24') >
+                        ipaddress.ip_interface('1.1.1.2/16'))
+
+        self.assertTrue(ipaddress.ip_interface('::1/64') ==
+                        ipaddress.ip_interface('::1/64'))
+        self.assertTrue(ipaddress.ip_interface('::1/64') <
+                        ipaddress.ip_interface('::1/80'))
+        self.assertTrue(ipaddress.ip_interface('::1/64') <
+                        ipaddress.ip_interface('::2/64'))
+        self.assertTrue(ipaddress.ip_interface('::2/48') <
+                        ipaddress.ip_interface('::1/64'))
+        self.assertTrue(ipaddress.ip_interface('::1/80') >
+                        ipaddress.ip_interface('::1/64'))
+        self.assertTrue(ipaddress.ip_interface('::2/64') >
+                        ipaddress.ip_interface('::1/64'))
+        self.assertTrue(ipaddress.ip_interface('::1/64') >
+                        ipaddress.ip_interface('::2/48'))
 
     def testNetworkComparison(self):
         # ip1 and ip2 have the same network address
diff --git a/Misc/NEWS b/Misc/NEWS
index 766bbb03d5d3aa..3fb908a74746d0 100644
--- a/Misc/NEWS
+++ b/Misc/NEWS
@@ -56,6 +56,9 @@ Extension Modules
 Library
 -------
 
+- bpo-29931: Fixed comparison check for ipaddress.ip_interface objects.
+  Patch by Sanjay Sundaresan.
+
 - [Security] bpo-29591: Update expat copy from 2.1.1 to 2.2.0 to get fixes
   of CVE-2016-0718 and CVE-2016-4472. See
   https://sourceforge.net/p/expat/bugs/537/ for more information.